Chemistry of Heterocyclic Compounds 2017, 53(9), 1014–1025
crystals, mp 171–172°С. IR spectrum, ν, cm–1: 3400 (NH),
J = 3.5, J = 0.7, H-3 Fur); 6.65 (1H, s, H-6); 7.16 (1H, dd,
J = 1.7, J = 0.7, H-5 Fur); 7.35–7.42 (4H, m, H Ar); 7.43–
7.45 (5H, m, H Ph). 13C NMR spectrum, δ, ppm: 30.1;
111.8; 112.1; 113.6; 119.3; 125.0; 127.8; 127.9; 128.8;
129.9; 130.1; 131.3; 136.7; 136.9; 139.1; 143.8; 145.7;
148.9; 196.5. Found, %: C 60.35; H 3.62; N 5.93.
C24H17BrN2O4. Calculated, %: C 60.39; H 3.59; N 5.87.
(4-Bromophenyl)[3-(furan-2-yl)-5-hydroxy-2-nitrobi-
phenyl-4-yl]methanone (23d). Yield 13%, colorless
crystals, mp 210–211°С. IR spectrum, ν, cm–1: 3239 (NH),
1656 (C=O), 1530, 1364 (NO2). 1Н NMR spectrum, δ, ppm
(J, Hz): 6.10 (1H, dd, J = 3.1, J = 2.0, H-4 Fur); 6.38 (1H,
dd, J = 3.1, J = 0.9, H-3 Fur); 7.14 (1H, s, H-6); 7.15 (1H,
dd, J = 2.0, J = 0.9, H-5 Fur); 7.36–7.40 (4H, m, H Ar); 7.41–
7.47 (5H, m, H Ph); 9.57 (1H, br. s, OH). 13C NMR
spectrum, δ, ppm: 112.3; 114.0; 119.5; 119.8; 125.0; 127.8;
127.9; 128.9; 129.4; 129.9; 131.3; 135.3; 136.3; 140.3; 142.4;
144.4; 144.9; 159.3; 197.8. Found, %: C 59.48; H 3.05; N 3.08.
C23H14BrNO5. Calculated, %: C 59.50; H 3.04; N 3.02.
[3-(Furan-2-yl)-5-(methylamino)-2-nitrobiphenyl-4-yl]-
(1-naphthyl)methanone (23e). Yield 87%, yellow
crystals, mp 160–161°С. IR spectrum, ν, cm–1: 3400 (NH),
1640 (C=O), 1525, 1360 (NO2). 1Н NMR spectrum, δ, ppm
(J, Hz): 2.95 (3H, s, NHCH3); 5.65 (1H, dd, J = 3.5, J = 1.9,
H-4 Fur); 6.10 (1H, dd, J = 3.5, J = 0.8, H-3 Fur); 6.64
(1H, dd, J = 1.9, J = 0.8, H-5 Fur); 6.71 (1H, s, H-6); 6.72
(1H, br. s, NH); 7.20–7.23 (1H, m, H Ar); 7.30–7.33 (7H, m,
H Ar, H Ph); 7.56–7.61 (1H, m, H Ar); 7.75–7.79 (2H, m,
H Ar); 8.57–8.61 (1H, m, H Ar). 13C NMR spectrum,
δ, ppm: 30.1; 111.1; 112.0; 112.1; 120.9; 123.7; 125.6;
126.1; 126.2; 127.5; 127.9; 128.3; 128.7; 128.8; 128.9;
130.4; 132.6; 133.7; 136.2; 137.0; 139.2; 139.6; 144.2;
146.4; 149.9; 199.1. Found, %: C 74.96; H 4.52; N 6.20.
C28H20N2O4. Calculated, %: C 74.99; H 4.50; N 6.25.
1
1640 (C=O), 1550, 1370 (NO2). Н NMR spectrum, δ, ppm
(J, Hz): 2.84 (3H, s, NHCH3); 3.79 (3H, s, OCH3); 5.45
(1H, br. s, NH); 6.09 (1H, dd, J = 3.5, J = 1.6, H-4 Fur); 6.32
(1H, dd, J = 3.5, J = 0.8, H-3 Fur); 6.61 (1H, s, H-6); 6.72–
6.77 (2H, m, H Ar); 7.17 (1H, dd, J = 1.6, J = 0.8, H-5
Fur); 7.41–7.46 (5H, m, H Ph); 7.59–7.63 (2H, m, H Ar).
13C NMR spectrum, δ, ppm: 30.2; 55.4; 111.5; 111.6;
112.9; 113.4; 121.2; 124.3; 127.9; 128.6; 128.7; 130.2;
131.4; 137.2; 138.4; 139.2; 143.7; 146.0; 148.3; 163.6;
195.8. Found, %: C 70.12; H 4.75; N 6.50. C25H20N2O5.
Calculated, %: C 70.09; H 4.71; N 6.54.
[3-(Furan-2-yl)-5-hydroxy-2-nitrobiphenyl-4-yl](4-meth-
oxyphenyl)methanone (23b). Yield 15%, colorless
crystals, mp 211–212°С. IR spectrum, ν, cm–1: 3194 (OH),
1
1640 (C=O), 1530, 1360 (NO2). Н NMR spectrum, δ, ppm
(J, Hz): 3.79 (3H, s, OCH3); 6.08 (1H, dd, J = 3.6, J = 1.9,
H-4 Fur); 6.38 (1H, dd, J = 3.6, J = 0.8, H-3 Fur); 6.70–
6.75 (2H, m, H Ar); 7.11 (1H, s, H-6); 7.15 (1H, dd,
J = 1.9, J = 0.8, H-5 Fur); 7.41–7.47 (5H, m, H Ph); 7.54–
7.58 (2H, m, H Ar); 9.23 (1H, br. s, OH). 13C NMR spectrum,
δ, ppm: 55.4; 112.0; 113.4; 113.5; 119.5; 120.8; 124.7;
127.9; 128.9; 129.2; 130.0; 131.3; 135.5; 139.4; 142.3;
144.3; 145.3; 158.5; 163.5; 196.8. Found, %: C 69.44;
H 4.12; N 3.42. C24H17NO6. Calculated, %: C 69.39;
H 4.12; N 3.37.
(4-Chlorophenyl)[3-(furan-2-yl)-5-(methylamino)-
2-nitrobiphenyl-4-yl]methanone (22c). Yield 70%, yellow
crystals, mp 185–186°С. IR spectrum, ν, cm–1: 3450 (NH),
1660 (C=O), 1525, 1360 (NO2). 1Н NMR spectrum, δ, ppm
(J, Hz): 2.87 (3H, d, J = 3.9, NHCH3); 5.92 (1H, br. s,
NH); 6.08 (1H, dd, J = 3.6, J = 1.9, H-4 Fur); 6.30 (1H, dd,
J = 3.6, J = 0.6, H-3 Fur); 6.65 (1H, s, H-6); 7.16 (1H, dd,
J = 1.9, J = 0.6, H-5 Fur); 7.19–7.23 (2H, m, H Ar); 7.42–
7.46 (5H, m, H Ph); 7.47–7.53 (2H, m, H Ar). 13C NMR
spectrum, δ, ppm: 30.1; 111.8; 112.0; 113.5; 119.4; 124.9;
127.9; 128.3; 128.7; 128.8; 130.0; 136.3; 136.9; 139.0;
139.1; 139.2; 143.8; 145.8; 148.9; 196.3. Found, %:
C 66.64; H 3.95; N 6.52. C24H17ClN2O4. Calculated, %:
C 66.59; H 3.96; N 6.47.
This study was performed with financial support from
the Russian Foundation for Basic Research and the
Ministry of Education of the Omsk Region (grant 16-43-
550144r_a).
References
(4-Chlorophenyl)[3-(furan-2-yl)-5-hydroxy-2-nitrobi-
phenyl-4-yl]methanone (23c). Yield 20%, colorless
crystals, mp 194–195°С. IR spectrum, ν, cm–1: 3398 (OH),
1640 (C=O), 1525, 1365 (NO2). 1Н NMR spectrum, δ, ppm
(J, Hz): 6.09 (1H, dd, J = 3.5, J = 1.7, H-4 Fur); 6.38 (1H,
dd, J = 3.5, J = 0.6, H-3 Fur); 7.14 (1H, s, H-6); 7.15 (1H,
dd, J = 1.7, J = 0.6, H-5 Fur); 7.19–7.23 (2H, m, H Ar);
7.40–7.49 (7H, m, H Ar, H Ph); 9.55 (1H, br. s, OH).
13C NMR spectrum, δ, ppm: 112.2; 114.0; 119.5; 119.8;
124.9; 127.9; 128.3; 128.9; 129.4; 129.8; 135.3; 135.8;
139.1; 140.2; 142.4; 144.4; 144.9; 159.2; 197.6. Found, %:
C 65.77; H 3.40; N 3.30. C23H14ClNO5. Calculated, %:
C 65.80; H 3.36; N 3.34.
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(4-Bromophenyl)[3-(furan-2-yl)-5-(methylamino)-
2-nitrobiphenyl-4-yl]methanone (22d). Yield 71%,
yellow crystals, mp 208–209°С. IR spectrum, ν, cm–1: 3445
1
(NH), 1660 (C=O), 1525, 1360 (NO2). Н NMR spectrum,
2. (a) Youssef, D. T. A. J. Nat. Prod. 2001, 64, 839. (b) Dufour, J.;
Neuville, L.; Zhu, J. Chem.–Eur. J. 2010, 16, 10523.
δ, ppm (J, Hz): 2.88 (3H, s, NHCH3); 5.94 (1H, br. s, NH);
6.08 (1H, dd, J = 3.5, J = 1.7, H-4 Fur); 6.30 (1H, dd,
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